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Simeoni is known for his maverick actions. During the stage win in the Vuelta he stopped just before the finish line and walked across the finish line with his bike in his hands. He did so as a tribute to the victims of the September 11, 2001 attacks. Later the Union Cycliste Internationale fined him for this.

In May 2009 he returned his Italian Championship jersey as a protest after his team was not invited to the 2009 Giro d'Italia.[2]

More famous is Simeoni's argument with Lance Armstrong. Simeoni was treated by doctor Michele Ferrari, who was also Armstrong's doctor. Simeoni testified in court that he began doping in 1993, that Dr. Ferrari had prescribed him doping products such as EPO and Human Growth Hormone in 1996 and 1997, and that Ferrari also gave him instructions on how to use these products.[3] In 2001 and 2002 Simeoni was suspended for several months for doping use. Armstrong reportedly called Simeoni a "liar" in an interview with the French newspaper Le Monde in July 2003. Simeoni lodged a charge of defamation against Armstrong and demanded €100,000. Simeoni announced that he would give any money awarded to him to charity.

On the 18th stage of the 2004 edition of the Tour de France, Simeoni gapped up to a breakaway of six riders that posed no threat to Armstrong's leading position. Nevertheless, Armstrong followed Simeoni, which prompted Armstrong's rival T-Mobile Team to try to catch the breakaway. This would not only catch Simeoni but also eliminate the stage winning chances of the six riders in the original breakaway. The six riders implored Armstrong to drop back to the peloton, but Armstrong would not go unless Simeoni went with him and the two riders dropped back to the peloton.[4] When Simeoni dropped back, he was abused by other riders, including Andrea Peron, Filippo Pozzato and Giuseppe Guerini. In a later interview, he told of how Daniele Nardello also abused him, calling him "a disgrace".[5] Afterwards, Armstrong made a "zip-the-lips" gesture but later said that Simeoni "did not deserve" to win a stage. Two days later was the final stage, which is usually a slow stage in which the Tour winner (in 2004 it was Armstrong) already celebrates his victory. But in this stage Simeoni continuously attacked, to take revenge for what Armstrong did three days before, but was reeled in every time by Armstrong's team.[6] Simeoni was again insulted and spat at by other riders after this.

Because Simeoni was a prosecution witness in legal proceedings against Ferrari at the time of Armstrong's move against him in the 2004 Tour, Italian authorities threatened to bring charges of witness intimidation against Armstrong. In March 2005 Armstrong was interviewed by the authorities, apparently without resolution. Armstrong had been indicted by Italian authorities in December 2005 and ordered to stand trial for defaming Simeoni on March 7, 2006. In April 2006, the defamation charges were dropped.[7]

In October 2012, Armstrong was stripped of all seven of his Tour titles and banned from cycling for life. In January 2013, he admitted to doping. Simeoni's reaction to Armstrong's confession was: "I acknowledge Armstrong's confession on television but he put me through such a humiliating experience and damaged me so much, in terms of sport, morale and finances that I don't know if I could ever forgive him."[8]